Hydrogen Peroxide → Trifluoromethyluracil

HRID 1363438Notes

Reaction equation

HRID 1363438 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].S(=O)(=O)(O)O.[F:14][C:15](I)([F:17])[F:16].OO>S([O-])([O-])(=O)=O.[Fe+2].CS(C)=O>[F:14][C:15]([F:17])([F:16])[C:7]1[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1][CH:8]=1

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 1174UracilHCID 16843Trifluoroiodomethane

Product 1

HCID 5899TrifluoromethyluracilYield 97%

Reagents, catalysts & solvents 2

HCID 24393Ferrous SulfateCatalystHCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
65 °C

Procedure

11.2 g (100 mmol) of uracil was weighed and placed in a 300 ml two-neck flask equipped with a magnetic rotor and the atmosphere in the flask was replaced with argon. The following materials were added thereinto: 80 ml of dimethyl sulfoxide, 0.55 ml of concentrated sulfuric acid, 245 mmol of trifluoromethyl iodide, 20 ml of a 30% hydrogen peroxide aqueous solution and 10 ml of a 1.5 mol/l aqueous solution of iron (II) sulfate. The mixture was stirred at 60 to 70° C. for 100 minutes and then the resulting solution was cooled to room temperature. Formation of 5-trifluoromethyluracil (19F-NMR yield: 97%) was confirmed in the same manner as in Example 1.

Workup

  1. customplaced in a 300 ml two-neck flask
  2. customequipped with a magnetic rotor
  3. additionThe following materials were added
  4. temperaturethe resulting solution was cooled to room temperature

Sources & evidence

ORD record
ord-d7016c9a239c4b21a849d404be5a186f
Source dataset
uspto-grants-2011_02
Patent number
US07884202B2

Reaction notes

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